The Lost Art of the Itinerary

Call me nostalgiac, but I remember the days when any travel agency that you paid to make trip arrangements actually provided a coherent document detailing said arrangements.

Apparently this is Old School. Online booking sites these days are taking an entirely new approach.

Instead of confirming all the details of your forthcoming dream trip that you have just spent the last 168 agonizing minutes of your life hunting down and purchasing – they will helpfully introduce two separate ways to review the information they are not actually providing on the first screen of your online booking confirmation, and remind you of your missed opportunity to make associated travel arrangements through their site… in return for which they will provide you substantial, (and completely unverifiable,) savings.

In fact, it isn’t until you scroll down to the third screen, that interesting details like the flight number, when the flight departs and from where … magically appear. I don’t know about you, but I like to be really clear on where I need to be, and when. Call me OCD, but punctuality… particularly when many personal dollars are involved, feels Pretty Darned Important.

Just to make sure I wasn’t missing anything, I clicked the “See your itinerary” button… which led me to the same message we’re seeing in my email (above). Not terribly helpful.

Allow me to introduce Exhibit A – a semi-ideal itinerary:

Notice the subtle intricacies of an actual itinerary. You can see at a glance where you need to be, and when – and just in case you need to print out a boarding pass at the airport, the flight number! You can see the second leg of your trip. You can see things like whether a rental car and hotel have been booked (or not). More importantly, you can see when you’re returning, and from which airport (just in case it happens to be a different place than your departure). All of this allows you to figure out if you (or your support person) accidentally booked yourself to check in at a hotel the day after you arrive at your destination, or set you up to “pick up” a rental car 15 miles away from the airport, or there is a scheduled taxi strike the day you return. It happens.

In truth, you’re not going to get gate confirmations until the day of the trip. But dates, cities, airlines, and times… yeah. That should all be on the ‘page at a glance’ itinerary you get from your (and I’m using this term ironically) online quote travel agency unquote.

So why is this no longer considered the best way to provide customer service? As far as I can tell, the online booking site’s “itinerary” is designed to make the customer consider whether a real live Travel Agent might provide better service for the same fee the site is adding to your tickets and reservations. Imagine… a person… more importantly, a person with expertise on saving you money and making your trip more fabulous.

I recognize that these sites are programmed… to optimize cash flow… and reward shareholders. But that is not why their customers use them. The communication provided after the transaction is just as important as the information provided while the traveler is figuring out how to get from Point A to Point B. My advice, solicited or otherwise is, stop sending poorly constructed confirmation messages designed entirely to get the customer to buy something else. Send a freaking itinerary, okay?

This is why some slick new .com is already working on wiping the current slate of booking sites off the travel arrangement map. People working on setting up a memorable trip want more than digital promises of discounts. They want more than theoretical savings. They want to make sure they have made travel arrangements that ensure a trip full of joy, comfort, and beautiful experiences. They want to know that their great airline ticket deal is not going to result in ten days of jet-lagged regret. Most of all, they want a coherent presentation of the information they need to make sure they go to the right airport on the correct day, well in advance of the time their booked flight leaves. Just saying.


Needless to say, no one is paying me for my opinion here. This is just my advice as a customer, and a person who voluntarily travels a lot. If you’ve booked a trip online recently, what was it like? Did you find a site that provided a reasonably coherent itinerary? Share the love in the comments below.

Cheap Flights

I know all those travel booking sites promise you the best prices… and they are a good place to start. 

However, if you are following my advice on obtaining frequent flier status with an airline, you may need to weigh the savings against the loss of points counting toward status. 

Also you may find a better flight (departure time, number of stops) on the airline site itself than you find on any of the aggregator sites.  Not every airline releases all their seats to those resale sites.  They make more money selling flights direct to their customers, especially their frequent travelers, because they’re not allocating a fee to the ‘retailer’.  So price it both ways (on the resale site and on the airline’s site).

The best way to get the lowest possible airline fares is to book 7 weeks out.  That’s the magic number.  Don’t ask me why.  I’ve tested it repeatedly and if you book further out (say, 12 weeks) or too close to the departure date (3 weeks)… you will begin to see a pattern.  If you book flights for a business professional, or book them for yourself… and saving money is a major factor, this is what you do.  Plan ahead.  Just not THAT far ahead.  7 weeks… not 6, not 8.  [see me shrugging]

Another tip when flying places that don’t have a major hub (think Los Angeles, San Francisco, Paris, London, Chicago, New York, Singapore) is to consider booking the segments yourself.  For example, I could try to book a flight from Los Angeles to Lisbon.  The prices will generally run me around $1200 USD (all prices in USD unless otherwise noted), and there will be at least one stop, possibly two.  On the other hand, if I book (7 weeks out), a round trip from Los Angeles to London (LHR – Heathrow) I can get a major deal of $600-$700.  Add a round trip from London to Lisbon for another $200, and I’ve saved myself $200-$300 – per person. It adds up.

When trying to reach cities with even smaller airports like say… Palm Springs, CA USA… consider flying to Los Angeles (LAX) and renting a car or taking a Tesla Loop shuttle to Palm Springs.  In other words, you don’t have to fly directly to your final destination.  You might spend four hours waiting for the next flight, and spend another $400-600 on the airline ticket price when you could have rented a car for a week for $280 and driven 2 hours there, and 2 hours back… while enjoying the freedom of driving wherever you feel like going without paying for a driver.  It seems a bit complicated, but you have to factor in how much you love spending big dollars on mediocre wine at an airport vs. the chance to see the countryside, and the actual distances between the larger airport and the smaller regional airport. Cars also give you the chance to stop when and where you please, take pictures, and visit special attractions along the way. 

This is especially true for holiday trips when sight seeing and exploration are more important than how fast you get to your destination.  So flying into Paris’ Charles de Gaulle (CDG) airport and taking the train to Barcelona Spain might be more enjoyable than a direct flight from CDG to BCN. Of course you have to get back to Paris and one way tickets are universally more expensive than half a round trip so you have to drive or take the train back.  

Which brings me to item number 3.  A round trip ticket on one airline may be cheaper than a one way ticket on another.  Or possibly even on the same airline.  So price both options.  

How to Get the Cheapest Airline Tickets

I know all those travel booking sites promise you the best prices… and they are a good place to start. 

However, if you are following my advice on obtaining frequent flier status with an airline, you may need to weigh the savings against the loss of points counting toward status. 

Also you may find a better flight (departure time, number of stops) on the airline site itself than you find on any of the aggregator sites.  Not every airline releases all their seats to those resale sites.  They make more money selling flights direct to their customers, especially their frequent travelers, because they’re not allocating a fee to the ‘retailer’.  So price it both ways (on the resale site and on the airline’s site).

The best way to get the lowest possible airline fares is to book 7 weeks out.  That’s the magic number.  Don’t ask me why.  I’ve tested it repeatedly and if you book further out (say, 12 weeks) or too close to the departure date (3 weeks)… you will begin to see a pattern.  If you book flights for a business professional, or book them for yourself… and saving money is a major factor, this is what you do.  Plan ahead.  Just not THAT far ahead.  7 weeks… not 6, not 8.  [see me shrugging]

Another tip when flying places that don’t have a major hub (think Los Angeles, San Francisco, Paris, London, Chicago, New York, Singapore) is to consider booking the segments yourself.  For example, I could try to book a flight from Los Angeles to Lisbon.  The prices will generally run me around $1200 USD (all prices in USD unless otherwise noted), and there will be at least one stop, possibly two.  On the other hand, if I book (7 weeks out), a round trip from Los Angeles to London (LHR – Heathrow) I can get a major deal of $600-$700.  Add a round trip from London to Lisbon for another $200, and I’ve saved myself $200-$300 – per person. It adds up.

When trying to reach cities with even smaller airports like say… Palm Springs, CA USA… consider flying to Los Angeles (LAX) and renting a car or taking a Tesla Loop shuttle to Palm Springs.  In other words, you don’t have to fly directly to your final destination.  You might spend four hours waiting for the next flight, and spend another $400-600 on the airline ticket price when you could have rented a car for a week for $280 and driven 2 hours there, and 2 hours back… while enjoying the freedom of driving wherever you feel like going without paying for a driver.  It seems a bit complicated, but you have to factor in how much you love spending big dollars on mediocre wine at an airport vs. the chance to see the countryside, and the actual distances between the larger airport and the smaller regional airport. Cars also give you the chance to stop when and where you please, take pictures, and visit special attractions along the way. 

This is especially true for holiday trips when sight seeing and exploration are more important than how fast you get to your destination.  So flying into Paris’ Charles de Gaulle (CDG) airport and taking the train to Barcelona Spain might be more enjoyable than a direct flight from CDG to BCN. Of course you have to get back to Paris and one way tickets are universally more expensive than half a round trip so you have to drive or take the train back.  

Which brings me to item number 3.  A round trip ticket on one airline may be cheaper than a one way ticket on another.  Or possibly even on the same airline.  So price both options.  


Try these tips the next time you need to get away from it all. Let me know if they work for you… or if they don’t. Do you have a killer trick that works on a certain airline? Educate us! Drop a comment in the box below.